Thomas LeRoy Winebrenner

Thomas LeRoy Winebrenner


Thomas “Boss Hog” LeRoy Winebrenner, 82, of Cumberland passed away peacefully at home on April 6, 2022.

He was born in Frostburg, Md. on January 9, 1940 to the late George and Francis Winebrenner.

In addition to his parents he was also preceded in death by his wife of 43 years, Connie DeLozier Winebrenner and a brother, Bradley Leo Winebrenner.

Tom graduated from Beall High School in the class of 1957.

He worked briefly as an optician, which was how he met his wife, Connie, while fitting her for glasses. He then joined the Maryland State Police and served for approximately five years before transferring to the Maryland Department of Corrections, working there until his retirement as a Sergeant. He also worked as a constable with the Frederick County Sheriff’s Office (Md.).

“Boss Hog’s” hobbies revolved around motorcycles; having raced them, worked on them, and even a side business chrome plating them. He traveled extensively with his wife and son on many motorcycle trips across the country.

Tom was a Masonic Master Mason and a member of the Order of the Eastern Star and was also a member of the Blue Knights law enforcement motorcycle club.

Surviving is his son, Thomas “Tommy” Winebrenner and wife Maureen Murphy Winebrenner of Frederick; grandsons, Sean Thomas Winebrenner and Dylan Patrick Winebrenner; and his companion of over ten years, Paula Skidmore.

A private family service will be held and burial will be in Frostburg Memorial Park, Frostburg, Md.

Those wishing to make memorial contributions are asked to direct them to the National Law Enforcement Memorial Officers Fund at or 444 E Street NW, Washington, DC 20001.

Scarpelli Funeral Home, P.A. is assisting the family and condolences can be made at